Cool Boss Moves is a series where we share the tips, tricks, and strategies we stole from other great managers.
This week: Shadowing and sharing your work
Emma: It takes such a long time to get good at stuff. I have to remind myself of that all the time because so often the expectation is that everyone should be good at everything they do. It’s extra true on the job.
Andy: Yep, you get hired or promoted into a new role and it feels like you should automatically have all the skills and experience of someone who’s been doing it for years. We talk about this all the time in this newsletter. It’s basically the whole reason we started The Bent.
Emma: Yes! I know intellectually that people all around us are faking it ‘til they make it, but that doesn’t make it easier to ask for help on the things I assume I’m already supposed to know. Which is why I think it’s a particularly cool Cool Boss Move to offer to casually sit down and walk through the basics.
I’m thinking back to one of our 1-on-1s, Andy, when you plunked down a huge packet of paper and asked, “Wanna see this budget proposal I worked on 3 years ago?”
Andy: I remember that. I also remember saving that report thinking, “Surely, this thing that I am really proud of will be useful to me again one day.” I’d come across it while cleaning out old boxes of paperwork in my closet. Immediately, I wondered if you’d want to see it. You were hungry to learn, and I was always on the quest for things that would be interesting to you.
Emma: We spent an hour walking through the structure of the document, the argument, how you came up with all the numbers, the feedback it got, what you learned and did differently on later proposals. It was low-key and no pressure — you weren’t quizzing me, no one was performing. And, at the time, it wasn’t even all that relevant! It was like you were coaching a future version of me battling the panic shakes while writing my first major report on a deadline.
Andy: My own experience was one place I turned to figure out, What does Emma need to know next? I followed the course of my own development. It’s kind of like if I needed to start teaching third grade tomorrow, I could think back to my own experience and compile some ideas: long division, popcorn reading, guessing how many jelly beans are in a jar. It’s not a perfect way to figure out a curriculum, but it’s quick and if they’ve never guessed how many jelly beans are in a jar, then hey, they’re learning something new. As a manager, you don’t have to be a genius. You just have to be willing to share what you know with someone who’s interested.
Emma: And that’s key for this kind of learning: they need to want to know the things you know. Otherwise you’re just lecturing.
Andy: You should be able to see the sparkle of 100% YES MOST DEFINITELY in their eyes when you make the offer. I’ve been on both sides of this: “Yes, please, I’m dying to know how you manage your to-do list!” and “No, stop, I could care less about your methodology for flagging inbox messages.”
My yes’s usually have three things in common: I think the person is good at what they’re showing me; I believe I will use that skill some day; and I actually want to grow in that space.
Emma: This Cool Boss Move takes a real nosedive the second we start using it to micromanage or to lecture on how we think someone *should* be doing something they aren’t doing right now. It’s gotta be totally optional to work. No expectations.
Andy: Yeah, it’s not all that realistic to have someone shadow you once, and then assume they’ve mastered it. I’ve talked about one of my excellent managers, Caroline, before. She knew what she was doing — Harvard MBA, a “My spreadsheets are awesome” mug on her desk. I had an MFA in fiction writing, and no such mug. She’d explain where other spreadsheets, ones built by lesser mortals, went wrong: Why cells shouldn’t be collapsed vertically, why their formulas weren’t working properly. Can I remember everything she showed me? No, but after the first time, it was so easy to walk down the hall to her office, stand there holding my own spreadsheets, and ask her to go over it again. Her tour was an introduction, an overview, and an ongoing invitation.
Emma: This is trust-building! There’s something so remarkable about cracking the manager sheen and learning their thought process in real time. Seeing them make mistakes and have to Command+Z undo. Hearing the stories of how they learned XYZ trick, or the time they got kudos for doing ABC. It’s really cool, super intimate stuff.
Andy: And I love that this kind of learning takes place outside of the deadlines. The payoff, months down the road, is so rewarding — one of those rare moments when you feel like you prepared your team in advance. What sweet victory.
A Quick-Start Guide for Hosting a Shadowing Session
Want to give this Cool Boss Move a try? Here’s how to get started.
1. You need a willing (and very interested) audience.
You probably already have an idea of who on your team will perk up at something like this. They tend to be high performers, hungry for growth, and/or very interested in the concept of “skills.”
Start by asking if they’re interested. If they say yes, but you don’t see that 100% YES MOST DEFINITELY sparkle, try doing a quick mini version in 5 minutes and let them know you could go into more depth another time if they’re interested. Then, leave it in their court.
Note: This technique is for optional extra growth, not performance management. If there’s someone on your team who needs to be better at something for their job, then feedback and non-optional training are in order. You might even need to have a Not-Fun Conversation.
2. You need an interesting project or example.
This should probably be something you feel fluent and confident in. (Muddling through something new side-by-side as peers or collaborators is totally fine, it’s just a different move altogether.) Fluent and confident is different than “expert pro,” but you want to have a perspective you feel like you can coach to and back up with real reasoning. So, “I look at the average cost per click and multiply by the number of clicks to get an estimate on returns. We’ve seen that this is a good proxy for our actual returns in this category.” Not, “Well, you know, it’s part science, part art.”
Ideally this is also something core to the role or an inevitability — not a one-off your shadow may never experience. Different careers will probably cover different topics; some of our favorite shadowing opportunities include:
- Building useful spreadsheets
- Putting together a dashboard
- Hosting effective meetings
- Writing persuasive reports
- Knowing your numbers (and how to document them)
- Responding to demanding bosses / clients / teams / etc
- Giving feedback
- Designing an effective presentation style
- Resumes and cover letters 😀
- Productivity techniques or workflows
3. You need some time.
Forty-five minutes to an hour is nice. Too long and there’s no retention. Too short and you won’t have time to actually get to the meat. If there’s more to go over after the first session, you can always book another one. P.S. 1-on-1s are great for this!
4. *Optional* Sketch out what you’ll talk about.
The best part of shadow sessions is that they are largely unstructured. You can absolutely just plink around on your computer while someone watches and talk through what you’re doing. But if you’re someone who feels very stressed by that type of vulnerability, it’s nice to prepare with some talking points. We recommend 1–3 big takeaways. You can ask yourself, What makes this good? And, Why? Be prepared to have a point of view about it and describe concretely what you see.
5. Don’t get freaked if they ask you a challenging question. You can say something honest like, “Oh that’s interesting, I’ve never thought about that before.” Or, you can buy some time by saying something like, “Why do I put the headers in a frozen cell… Let me find a way to explain it.” The point isn’t to have a prepared slide show, but to have some footing and a willingness to think about their questions. In reality, you probably have all the answers if you give yourself a few moments to put words to them. Remember: they’re just trying to learn.